Ethanol → HCID 13649663, compound

HRID 280670Notes

Reaction equation

HRID 280670 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1.[N-:18]=[N+:19]=[N-:20].[Na+].C([OH:24])C>>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[C:4]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:18]=[N+:19]=[N-:20])=[CH:7][CH:6]=1)=[O:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 33557Sodium AzideHCID 23320950HCID 23320950, compound

Product 1

HCID 13649663HCID 13649663, compoundYield 98%

Procedure

A mixture of 4-(2,6-dichlorobenzyl)benzyl bromide (7.49 g, 21.8 mmol) and sodium azide (4.19 g, 64.5 mmol) in absolute ethanol (100 ml) was refluxed 5 hours, cooled, and evaporated under vacuum. The residue was triturated wit diethyl ether (100 ml), filtered, and evaporated under vacuum to provide 6.5 g (98%) 4-(2,6-dichlorobenzoyl)benzyl azide, m.p. 92°-94° C.

Workup

  1. temperaturewas refluxed 5 hours
  2. temperaturecooled
  3. customevaporated under vacuum
  4. customThe residue was triturated wit diethyl ether (100 ml)
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-dbddce9b31004799b4f583b89feacdcd
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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